US6872780B2 - Butyl polymer composition having improved cold flow properties - Google Patents

Butyl polymer composition having improved cold flow properties Download PDF

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US6872780B2
US6872780B2 US10/333,566 US33356603A US6872780B2 US 6872780 B2 US6872780 B2 US 6872780B2 US 33356603 A US33356603 A US 33356603A US 6872780 B2 US6872780 B2 US 6872780B2
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butyl polymer
parts
polymer
butyl
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US20040092665A1 (en
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Richard Pazur
Anthony J. Sumner
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Arlanxeo Canada Inc
Bayer AG
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Bayer Inc
Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
    • C08L23/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
    • C08L23/22—Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
    • C08L23/28—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by reaction with halogens or compounds containing halogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
    • C08L23/28—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by reaction with halogens or compounds containing halogen
    • C08L23/283—Halogenated homo- or copolymers of iso-olefins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/02—Homopolymers or copolymers of hydrocarbons
    • C08L25/04—Homopolymers or copolymers of styrene
    • C08L25/08—Copolymers of styrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof

Definitions

  • the present invention relates to a butyl polymer composition having improved cold flow properties. In another of its aspects, the present invention relates to a process for producing a butyl rubber vulcanizate having a desirable balance of properties, including improved air impermeability.
  • Butyl polymers have been known and commercially available for many years. They possess a variety of inherently satisfactory properties as elastomers which has enabled them to find utility in many commercial areas. Among their satisfactory inherent properties are their impermeability to air, high damping of low frequency vibrations and good resistance to aging, heat, acids, bases, ozone and other chemicals, after vulcanization. These properties render butyl polymers well suited for use in a variety of applications including articles requiring low or reduced permeability to air. Non-limiting examples of such applications include tire inner tubes, tire curing bladders and various air bladders.
  • Halogenated butyl polymers have also been known and commercially available for many years. In addition to possessing the satisfactory inherent properties of butyl polymers described above, halogenated butyl polymers also possess cure compatibility with more highly unsaturated rubbers and good adhesion to such other rubbers after vulcanization, which renders them well suited for use in pneumatic tire inner liners.
  • butyl rubber which is commercially important is resistance to cold flow. Specifically, users of butyl rubber typically will calendar the polymer into continuous very long sheets.
  • the polymer may be premixed with one or more of a filler (e.g., carbon black), a plasticizer, a tackifier, an extender oil and the like—such a composition may be characterized as a vulcanizable composition.
  • the calendar sheets are produced, it is quite common to reversibly fold or “wig-wag” the sheets on a pallet such that the height of the folded sheet is a number of feet.
  • the vulcanizable composition is susceptible to cold flow during shipping or storage, the weight of the folded polymer sheet causes the surface coating of the sheet (particularly at the bottom of the pile) to break, allowing adjacent fresh surfaces to contact, which leads to sticking of the sheets. This problem is exacerbated during long transportation or storage times, and/or high ambient temperatures. By the time the vulcanizable composition is ready for further processing it is more difficult to remove as a single sheet compared to the manner in which it was placed on the pallet.
  • U.S. Pat. No. 4,754,793 (Mohammed) teaches butyl elastomer compositions having reduced permeability to gases. Specifically, there is taught a rubber composition comprising a butyl polymer, an ⁇ -methylstyrene homopolymer, carbon black in a curing system, and optionally, a hydrocarbon extender oil.
  • a rubber composition comprising a butyl polymer, an ⁇ -methylstyrene homopolymer, carbon black in a curing system, and optionally, a hydrocarbon extender oil.
  • ⁇ -methylstyrene homopolymer is not available in quantities commercially significant to be used as an additive in butyl polymer compositions.
  • the principal reason may be attributed to a toughening of environment laws which had the effect of making it impractical to produce large quantities of the material for use as an additive as contemplated by Mohammed. Accordingly, while the teachings of Mohammed are useful, the commercial significance thereof is restricted somewhat by the unavailability of significant commercial quantities of ⁇ -methylstyrene homopolymer.
  • butyl polymer composition having improved cold flow properties and a desirable balance of other properties, such as air impermeability, green strength and processability.
  • the present invention provides a butyl polymer composition having improved cold flow properties, the composition comprising a butyl polymer and a styrene resin, the styrene resin comprising a first copolymer of ⁇ -methylstyrene and another styrenic monomer.
  • FIGS. 1-14 illustrate various physical properties of polymer compositions and of vulcanizates derived therefrom produced in the Examples set out below.
  • butyl polymer “butyl rubber” and “butyl rubber polymer” are used interchangeably throughout this specification and are intended to mean a polymer prepared by reacting a major portion of an isoolefin monomer with a minor portion of a multiolefin monomer.
  • the butyl polymer comprises a copolymer of a C 4 to C 8 monoolefin monomer and a C 4 to C 14 multiolefin monomer.
  • the preferred C 4 to C 8 monoolefin comprises an isomonoolefm.
  • useful monoolefin monomers may be selected from the group comprising isobutylene, 2-methyl-1-butene, 3-methyl-1 -butene, 2-methyl-2-butene, 4-methyl- I -pentene and mixtures thereof.
  • the butyl polymer may be derived from a mixture comprising from about 70 to about 99.5 parts by weight of the C 4 to C 8 monoolefin monomer and from about 30 to about 0.5 parts by weight of the C 4 to C 14 multiolefin monomer. More preferably, the butyl polymer is derived from a mixture comprising from about 80 to about 99.5 parts by weight of the C 4 to C8 monoolefin monomer and from about 20 to about 0.5 parts by weight of the C 4 to C 14 multiolefin monomer.
  • the most preferred butyl polymer for use in the present butyl polymer composition is derived from a mixture comprising from about 97 to about 99.5 parts by weight of isobutylene and from about 3 to about 0.5 parts by weight of isoprene.
  • a particularly preferred class of butyl polymers for use in the present butyl polymer composition is the class of halogenated butyl polymers, particularly chlorinated butyl polymers and brominated butyl polymers.
  • the halogenated butyl polymer comprises a halogen in the amount of from about 0.1 to about 8% by weight of the polymer. More preferably, the halogenated butyl polymer comprises a halogen in the amount of from about 0.5 to about 4% by weight of the polymer. Most preferably, the halogenated butyl polymer comprises a halogen in the amount of from about 1.5 to about 3.0% by weight of the polymer.
  • the halogenated butyl polymer may be produced by halogenating a previously produced butyl polymer in a conventional manner. See, for example, U.S. Pat. No. 5,886,106.
  • the halogenated butyl rubber may be produced either by treating finely divided butyl rubber with a halogenating agent, such as chlorine or bromine, preferably bromine, or by producing brominated butyl rubber by the intensive mixing, in a mixing apparatus, of brominatiug agents such as N-bromosuccinimide with a previously made butyl rubber.
  • the halogenated butyl rubber may be produced by treating a solution or a dispersion in a suitable organic solvent of a previously made butyl rubber with corresponding brominating agents. See, for more detail, Ullmann's Encyclopedia of Industrial Chemistry (Fifth, Completely Revised Edition, Volume A23; Editors Elvers et al.). The amount of halogenation during this procedure may be controlled so that the final polymer has the preferred amounts of halogen described hereinabove.
  • Another component of the present butyl polymer composition is a styrene resin comprising a first copolymer of ⁇ -methylstyrene and another styrenic monomer.
  • the other styrenic monomer is selected from the group comprising styrene, vinyl styrene, p-methylstyrene (vinyl toluene), p-chlorostyrene, p-methoxystyrene, indene, indene derivatives and mixtures thereof.
  • the most preferred styrenic monomer may be selected from the group comprising styrene, p-methylstyrene and mixtures thereof. Copolymers of ⁇ -methylstyrene and such styrenic monomers are known and thus are within the purview of a person skilled in the art.
  • a copolymer of ⁇ -methylstyrene and styrene useful in the present invention is commercially available from Hercules Inc. under the tradename Kristalexg® 1120.
  • a copolymer of ⁇ -methylstyrene and vinyl toluene useful in the present is commercially available from Hercules Inc. under the tradename Piccotex® 120.
  • the styrene resin is present in an amount of up to about 25 parts by weight per hundred parts by weight butyl polymer. More preferably, the styrene resin is present in an amount in the range of from about 5 to about 20 parts by weight per hundred parts by weight butyl polymer. Even more preferably, the styrene resin is present in an amount in the range of from about 5 to about 15 parts by weight per hundred parts by weight butyl polymer. Most preferably, the styrene resin is present in an amount in the range of from about 10 to about 15 parts by weight per hundred parts by weight butyl polymer.
  • the present butyl polymer composition further comprises a filler.
  • a filler The nature of the filler is not particularly restricted, and the choice of suitable fillers is within the purview of a person skilled in the art.
  • suitable fillers include carbon black (e.g., FEF, MT, GPF and SRF), clays, titanium dioxide, silica fillers (with or without unsaturated silanes), calcium carbonate, talc (magnesium silicate) and the like.
  • the amount of filler is conventional.
  • the filler is present in an amount in the range of from about 20 to about 200 parts by weight per hundred parts by weight of the polymer.
  • the filler is present in an amount in the range of from about 20 to about 100 parts by weight per hundred parts by weight of the polymer. Most preferably, the filler is present in an amount in the range of from about 40 to about 80 parts by weight per hundred parts by weight of the polymer.
  • the present butyl polymer composition may further comprise a hydrocarbon extender oil.
  • hydrocarbon extender oils are well known in the art. Suitable hydrocarbon extender oils include the paraffinic or naphthenic extender oils, preferably paraffinic. Also known in the art is that the use of such extender oils in butyl rubber vulcanizates generally causes the air permeability of such vulcanizates to increase. Thus, if used in the present butyl polymer composition, such hydrocarbon extender oils should be present in minor amounts.
  • the oil(s) is present in an amount of from 0 to about 7, preferably from 0 to about 4, parts by weight per hundred parts by weight butyl polymer in the composition.
  • the present butyl polymer composition may further comprise a curing system.
  • a curing system suitable for use is not particularly restricted and is within the purview of a person skilled in the art.
  • a typical curing system comprises: (i) a metal oxide, (ii) elemental sulfur and (iii) at least one sulfur-based accelerator.
  • metal oxides as a component in the curing system is well known in the art.
  • a suitable metal oxide is zinc oxide, which is typically used in the amount of from about 1 to about 10, preferably from about 2 to about 5, parts by weight per hundred parts by weight butyl polymer in the composition.
  • Elemental sulphur comprising component (ii) of the preferred curing system is typically used in amounts of from about 0.2 to about 2 parts by weight, per hundred parts by weight butyl polymer in the composition.
  • Suitable sulfur-based accelerators are typically used in amounts of from about 0.5 to about 3 parts by weight, per hundred parts by weight butyl polymer in the composition.
  • Non-limiting examples of useful sulfur-based accelerators may be selected from the thiuram sulfides such as tetramethyl thiuram disulfide (TMTD), the thiocarbamates such as zinc dimethyl dithiocarbamate (ZDC) and the thiazyl and benzothiazyl compounds such as mercaptobenzothiazyl disulfide (MBTS).
  • TMTD tetramethyl thiuram disulfide
  • ZDC zinc dimethyl dithiocarbamate
  • MBTS mercaptobenzothiazyl disulfide
  • the sulphur based accelerator is mercaptobenzothiazyl disulfide.
  • Stabilizeis, anti-oxidants and tackifiers may also be added in the usual way and in the normal amounts for compounding butyl-type rubbery polymers.
  • the procedure of mixing the various components of this invention is not specifically restricted.
  • all of the ingredients of the rubber composition described above may be mechanically mixed at an initial temperature of not more than about 80° C. in an internal mixer and then vulcanized in a conventional manner.
  • the butyl polymer and styrene resin may be solution blended, the blend recovered from solution prior to being mechanically mixed with the remaining ingredients and then vulcanized in a conventional manner.
  • a blend of a butyl polymer and styrene resin is suitably achieved using solutions of the polymers in mutually compatible hydrocarbon liquid solvents.
  • Such a blend may be recovered from solution by standard recovery techniques of solvent removal and drying, followed by the compounding and vulcanization procedure described above.
  • the styrene resin may be added, in bulk, to the butyl polymer during a final stage of the manufacturing process of the latter.
  • the polymers may be mixed with conventional compounding ingredients such as one or more of carbon black, hydrocarbon extender oil, tackifiers, stabilizers, processing aids and anti-oxidants. This results in the production of a vulcanizable composition which can be transported, stored and/or vulcanized.
  • conventional compounding ingredients such as one or more of carbon black, hydrocarbon extender oil, tackifiers, stabilizers, processing aids and anti-oxidants.
  • the vulcanizable composition may be cured in a conventional manner, for example, by heating for from about 5 to about 60 minutes at temperatures of from about 150° C. to about 200° C. to form elastomeric vulcanizates.
  • Example 2 With reference to FIG. 6 , it will be seen that the hot air aging properties of the vulcanizates produced in Examples 2 and 3 is similar to that in Example 1 (i.e., there is no apparent degradation of this property as a result of adding styrene polymer to the butyl polymer composition).
  • Example 4 contains no styrene resin and thus, this Example is provided for comparative purposes only.
  • Examples 5-14 contain various combinations of styrene resin and extender oil.
  • the combination of hydrocarbon extender oil and styrene polymer is useful in mediating the compound Mooney viscosity of the butyl rubber composition between the case where there is no styrene polymer additive and the case where there is no hydrocarbon extender oil additive.
  • a butyl polymer of the present invention has certain improved properties (such as green strength and cold flow) compared to compositions of the art with no deleterious effects on other important properties (such as permeability to air).
  • Example 1 Example 2
  • Example 3 BB 2030 100 100 100 Sunpar 2280 7 — — Kristalex ® 1120 — 10 — Piccotex ® 120 — — 10 N-660 60 60 60 Pentalyn “A” 4 4 4 Stearic Acid 1 1 1 MBTS 1.3 1.3 1.3 Sulfur 0.5 0.5 0.5 ZnO 3 3 3

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US10/333,566 2000-07-27 2001-07-24 Butyl polymer composition having improved cold flow properties Expired - Fee Related US6872780B2 (en)

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CA2315830 2000-07-27
CA002315830A CA2315830A1 (en) 2000-07-27 2000-07-27 Butylpolymer composition having improved cold flow properties
PCT/CA2001/001064 WO2002010277A1 (en) 2000-07-27 2001-07-24 Butyl polymer composition having improved cold flow properties

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EP (1) EP1311610A1 (ja)
JP (1) JP2004505153A (ja)
KR (1) KR20030045014A (ja)
CN (1) CN1461330A (ja)
AU (1) AU2001278317A1 (ja)
CA (1) CA2315830A1 (ja)
RU (1) RU2003105602A (ja)
TW (1) TWI227258B (ja)
WO (1) WO2002010277A1 (ja)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050222335A1 (en) * 2002-07-17 2005-10-06 Exxonmobil Chemical Paens Inc. Elastomeric blend for air barriers
US20070270538A1 (en) * 2006-05-19 2007-11-22 Marc Stacey Somers Elastomeric compositions comprising butyl rubber and propylene polymers

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8722806B2 (en) * 2008-02-15 2014-05-13 Bridgestone Corporation Rubber composition and tire using the same
JP5503159B2 (ja) * 2008-02-15 2014-05-28 株式会社ブリヂストン ゴム組成物及びそれを用いたタイヤ
JP5076977B2 (ja) * 2008-03-07 2012-11-21 横浜ゴム株式会社 空気入りタイヤ
MX2009010135A (es) * 2009-09-22 2011-03-22 Inst Mexicano Del Petroleo Star Formulacion de polimeros aleatorios para mejorar flujo de crudos del petroleo.
WO2016102319A1 (en) * 2014-12-23 2016-06-30 Arizona Chemical Company, Llc Inner liner composition comprising low acid number rosin esters
US10472502B2 (en) 2015-12-31 2019-11-12 Kraton Polymers U.S. Llc Resin-extended rubber composition and tire rubber compositions prepared therewith
JP2018012818A (ja) * 2016-07-22 2018-01-25 横浜ゴム株式会社 タイヤ用ゴム組成物
PL3765536T3 (pl) * 2018-03-16 2022-06-13 Fina Technology, Inc. Kompozycja polimerowa i zastosowanie do wytwarzania kleju oraz wyrób ją zawierający

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4284535A (en) * 1978-08-29 1981-08-18 The Goodyear Tire & Rubber Company Rubber composites suitable for tire sidewalls from hexadiene polymer
US4487892A (en) * 1982-03-30 1984-12-11 Bridgestone Tire Co., Ltd. Rubber compositions for use in tires
US4754793A (en) * 1987-06-23 1988-07-05 Polysar Limited Butyl elastomeric compositions having reduced permeability to gases
US5532312A (en) * 1990-08-15 1996-07-02 Exxon Chemical Patents, Inc. Tire sidewall composition
US5886106A (en) 1996-08-06 1999-03-23 Bayer Aktiengesellschat Halogenated butyl rubbers having a low halogen content
US6399710B1 (en) * 1997-11-20 2002-06-04 Advanced Elastomer Systems, L.P. Modification of thermolastic vulcanizates with a thermoplastic random copolymer of ethylene

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4284535A (en) * 1978-08-29 1981-08-18 The Goodyear Tire & Rubber Company Rubber composites suitable for tire sidewalls from hexadiene polymer
US4487892A (en) * 1982-03-30 1984-12-11 Bridgestone Tire Co., Ltd. Rubber compositions for use in tires
US4754793A (en) * 1987-06-23 1988-07-05 Polysar Limited Butyl elastomeric compositions having reduced permeability to gases
EP0296332A2 (en) 1987-06-23 1988-12-28 Polysar Limited Halobutyl elastomeric compositions
US5532312A (en) * 1990-08-15 1996-07-02 Exxon Chemical Patents, Inc. Tire sidewall composition
US5886106A (en) 1996-08-06 1999-03-23 Bayer Aktiengesellschat Halogenated butyl rubbers having a low halogen content
US6399710B1 (en) * 1997-11-20 2002-06-04 Advanced Elastomer Systems, L.P. Modification of thermolastic vulcanizates with a thermoplastic random copolymer of ethylene

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050222335A1 (en) * 2002-07-17 2005-10-06 Exxonmobil Chemical Paens Inc. Elastomeric blend for air barriers
US20070270538A1 (en) * 2006-05-19 2007-11-22 Marc Stacey Somers Elastomeric compositions comprising butyl rubber and propylene polymers

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WO2002010277A1 (en) 2002-02-07
US20040092665A1 (en) 2004-05-13
AU2001278317A1 (en) 2002-02-13
JP2004505153A (ja) 2004-02-19
EP1311610A1 (en) 2003-05-21
TWI227258B (en) 2005-02-01
CA2315830A1 (en) 2002-01-27
KR20030045014A (ko) 2003-06-09
RU2003105602A (ru) 2004-08-27
CN1461330A (zh) 2003-12-10

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